David Siegel, Former CEO of Meetup & Investopedia, on Solving the Loneliness Crisis, Rescuing Meetup from WeWork, and Why Israelis are Happier than Americans

On this episode of Invested, Michael Eisenberg sits down with David Siegel, former CEO of Meetup, former CEO of Investopedia, former President of Seeking Alpha, author of Decide & Conquer, and founder of the Israel Tech Mission.

David has spent more than 25 years building and leading technology companies, but his most passionate mission has been tackling one of society’s fastest-growing challenges: loneliness. As CEO of Meetup, he led the global community platform through a dramatic turnaround, transforming it from a money-losing business into a profitable company while helping millions of people connect around shared interests, passions, and causes.

In this wide-ranging conversation, Michael and David explore the roots of the loneliness epidemic, why social media and screens may be making people less connected than ever, and what can actually be done to rebuild community in modern society. David shares lessons from leading Meetup through COVID, selling multiple companies, scaling organizations, and retiring from full-time operating roles at age 50.

More on in the episode:

• Why loneliness is more dangerous than smoking

• How Meetup grew into a global community platform spanning nearly every country

• The surprising origin story of Meetup after 9/11

• Turning around a WeWork company losing $20 million annually

• Why social media increased loneliness instead of reducing it

• The cultural and technological drivers behind rising social anxiety

• Leadership lessons from building and selling companies

• The power of decision-making and creating your own luck

• Israel Tech Mission and bringing global tech leaders to Israel

• Why David believes mandatory national service is the best solution to the loneliness epidemic

• What Israel gets right about meaning, community, and belonging

David Siegel is the former CEO of Meetup, the largest platform for finding and building local community. He has had two exits over the last six years where he drove investor returns of 5x and 7x. Prior to Meetup, David served as CEO of Investopedia and President of Seeking Alpha. Today he advises CEOs, serves on boards, teaches strategy and scaling at Tel Aviv University, hosts the Keep Connected podcast, and leads the Israel Tech Mission, which has brought hundreds of global technology executives to Israel.

If you want to understand leadership, community, loneliness, company turnarounds, and what creates meaning in modern life, this episode is essential viewing.

Please rate this episode 5 stars wherever you stream your podcasts!

KEY TOPICS 

00:01 — Loneliness Worse Than Smoking?

02:03 — The Anti-Wall Street Career Path

05:04 — The DoubleClick Mafia Explained

08:23 — From HR to CEO

11:13 — How Michael Changed David's Career

13:27 — Adam Neumann's ‘27 Interviews’

16:36 — Retired at 50. Then What?

18:08 — Meetup Was Born After 9/11

21:36 — Fixing A $20M WeWork Money Pit

24:02 — Revenue Is Not Evil

27:15 — Why Young People Are Lonelier

29:21 — Meetup's Biggest Product Mistake

34:22 — The DEI Debate at Meetup

40:08 — October 7th Changed Everything

59:57 — Mandatory Service Ends Loneliness

RESOURCES

Follow David on Linkedin: https://www.linkedin.com/in/davidmsiegel/ 

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CREDITS

Executive Producer: Erica Marom 

Producer: Sofi Levak, Myron Shneider, Dalit Merenfeld

Video and Editing: Nadav Elovic 

Music and Creative Direction: Uri Ar 

Content and Editorial: Jackie Goldberg

Design: Nimrod Sapir